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Benson graduated from a community college in San Diego, California, before moving to Los Angeles to pursue an acting career.

While working as a stand-in and extra in movies and TV, such as a cousin in Curb Your Enthusiasm he did his first stand-up gig after he and two other friends dared each other to try it. One of them didn't show up, and the other had signed up too late. Benson claimed that "I went on anyway and did my three minutes of whatever I could come with and people actually laughed".[1] At the age of 22, Benson became a stand-up comedian.

Benson was part of the writing team that created (and performed in) The Marijuana-Logues. He was also named Stoner of the Year for 2006 by High Times Magazine. Benson also made his own documentary Super High Me, which was released on DVD on June 10, 2008.

Benson also appears on the comedy compilation CD Comedy Death-Ray. Benson released his first full-length solo comedy album, Professional Humoredian, on July 15th, 2008.

Benson hosts a podcast called I Love Movies which is recorded infront of a live audience at the Upright Citizens Brigade Theatre in Los Angeles, typically right before the Comedy Death Ray live show. The show usually airs biweekly, though not always. Benson's guests have included Sarah Silverman, Patton Oswalt, Brian Posehn, John Hamm, Adam Carolla, David Cross, Bob Odenkirk, Scott Aukerman and Paul F. Tompkins. A regular feature of the podcast is the Leonard Maltin Game, in which Benson reads the cast of an unknown movie in reverse order (star of the movie comes last) from Leonard Maltin's Movie Guide to his guests, who attempt to guess the movie.

On August 4, 2009, Benson's second CD, Unbalanced Load, was released by Comedy Central Records.

On March 17, 2009, Benson made jokes about the Canadian military's mission in Afghanistan, while appearing on the Fox News comedy program Red Eye w/ Greg Gutfeld. Greg Gutfeld, the host of the program also joked, among other things, that the United States should Invasion|invade Canada. These comments went largely unnoticed until a recording of the five minute clip was circulated on the Internet during March 2009, Canada's deadliest month in Afghanistan since arriving in 2002.[2] The Government of Canada demanded an apology from FOX News as well as the panelists for "...despicable, hurtful and ignorant comments."[3] On March 24th, Benson apologized for the remarks on CTV News Channel's Power Play with Tom Clark.[4]